Advances in Heterocyclic Chemistry, Vol. 5 by A.R. Katritzky, A.J. Boulton and J.M. Lagowski (Eds.)

By A.R. Katritzky, A.J. Boulton and J.M. Lagowski (Eds.)

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The agreement of theoretical indices with the course of substitution reactions and some physico-chemical properties is aatisfactory (1,254). r 12 sr FIG. 4. Free valence plotted against radical superdelocalizability for a group of benzo derivatives of thiophene (Model B2). Positions adjacent to a heteroabm are designated by solid symbols. 56 Experimental data for 2- and 3-nitrothiophenes are satisfactorily R. D. Brown in “Current Trends in HeterocyclicChemistry” (A. ) p. 13. Butterworths, London, 1958.

23, 11 (1960). 80 A. Luttringhaus and N. Engelhard, Angew. Chem. 73, 218 (1961). A. Luttringhaus and N. Engelhard, Chem. Ber. 93, 1525 (1960). 81 S. Smiles and T. P. Hilditch, J . Chem. 99, 145 (1910). 82 W. Bonthrone and D. H. Reid, Chem. Ind. (London) 1192 (1960). 83 A. Luttringhaus, N. Engelhard, and A. Kolb, Ann. Chem. 654, 189 (1962). 84 A. Luttringhaus and A. Kolb, 2. Naturforsch. 16b, 762 (1961). 77 78 24 [Sec. 11. 2. R. 82Models of cations 64-66 and 68 have been studied recently by (68) (67) the HMO and perturbation methods (Models A1 and B),16the thiapyrylium cation itself having been previously studied.

700W. E. Parham, H. Wynberg, W. R. Haaek, P. A. Howell, R. N. Curtis, and W. N. Lipscomb, J. Am. Chsm. 76,4957 (1954). 7 1 M. M. Kreevoy, J . Am. Chem. Soc. 80, 5643 (1958). 68 69 E. 22 [Sec. 11. l. R. ZAHRADN~K oxidizability of 1,4-dithiin. 72Solutions of thianthrene in acetic anhydride containing 1yo perchloric acid73or in 96-91yo HzS0474are paramagnetic; this is probably due to the presence of thianthrene radical cations (55) in (55) these media. This view is supported by a study of ESR, electronic, and near-infrared spectra.

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